Direct Azidation of Adamantane and Norbornane by Stable Azidoiodinanes

Alexei P. Krasutsky; Chris J. Kuehl; Viktor Zhdankin

doi:10.1055/s-1995-5173

Direct Azidation of Adamantane and Norbornane by Stable Azidoiodinanes

Alexei P. Krasutsky, Chris J. Kuehl, Viktor Zhdankin

Research output: Contribution to journal › Article › peer-review

61 Scopus citations

Abstract

Stable azidoiodinanes 1 and 2 react with norbornane, adamantane and 1,3-dimethyladamantane upon heating in the presence of catalytic amounts benzoyl peroxide with the formation of the respective azides 6-8 in moderate yields. In these reactions, reagent 2 can be generated in situ from 2-iodosobenzoic acid and azidotrimethylsilane, and used without isolation.

Original language	English (US)
Pages (from-to)	1081-1082
Number of pages	2
Journal	Synlett
Volume	1995
Issue number	10
DOIs	https://doi.org/10.1055/s-1995-5173
State	Published - Oct 1995
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by a Cottrell College Science Award of Research Corporation. Acknowledgement is also made to the Donors of The Petroleum Research Fund, administered by the ACS, and to the National Science Foundation (NSF/CHE-9505868) for partial support of this research.

Keywords

1-azidoadamantane
2-azidonorbornane
azides
azidoiodinane
iodine

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10.1055/s-1995-5173

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title = "Direct Azidation of Adamantane and Norbornane by Stable Azidoiodinanes",

abstract = "Stable azidoiodinanes 1 and 2 react with norbornane, adamantane and 1,3-dimethyladamantane upon heating in the presence of catalytic amounts benzoyl peroxide with the formation of the respective azides 6-8 in moderate yields. In these reactions, reagent 2 can be generated in situ from 2-iodosobenzoic acid and azidotrimethylsilane, and used without isolation.",

keywords = "1-azidoadamantane, 2-azidonorbornane, azides, azidoiodinane, iodine",

author = "Krasutsky, {Alexei P.} and Kuehl, {Chris J.} and Viktor Zhdankin",

note = "Funding Information: This work was supported by a Cottrell College Science Award of Research Corporation. Acknowledgement is also made to the Donors of The Petroleum Research Fund, administered by the ACS, and to the National Science Foundation (NSF/CHE-9505868) for partial support of this research.",

year = "1995",

month = oct,

doi = "10.1055/s-1995-5173",

language = "English (US)",

volume = "1995",

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T1 - Direct Azidation of Adamantane and Norbornane by Stable Azidoiodinanes

AU - Krasutsky, Alexei P.

AU - Kuehl, Chris J.

AU - Zhdankin, Viktor

N1 - Funding Information: This work was supported by a Cottrell College Science Award of Research Corporation. Acknowledgement is also made to the Donors of The Petroleum Research Fund, administered by the ACS, and to the National Science Foundation (NSF/CHE-9505868) for partial support of this research.

PY - 1995/10

Y1 - 1995/10

N2 - Stable azidoiodinanes 1 and 2 react with norbornane, adamantane and 1,3-dimethyladamantane upon heating in the presence of catalytic amounts benzoyl peroxide with the formation of the respective azides 6-8 in moderate yields. In these reactions, reagent 2 can be generated in situ from 2-iodosobenzoic acid and azidotrimethylsilane, and used without isolation.

AB - Stable azidoiodinanes 1 and 2 react with norbornane, adamantane and 1,3-dimethyladamantane upon heating in the presence of catalytic amounts benzoyl peroxide with the formation of the respective azides 6-8 in moderate yields. In these reactions, reagent 2 can be generated in situ from 2-iodosobenzoic acid and azidotrimethylsilane, and used without isolation.

KW - 1-azidoadamantane

KW - 2-azidonorbornane

KW - azides

KW - azidoiodinane

KW - iodine

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DO - 10.1055/s-1995-5173

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JO - Synlett

JF - Synlett

IS - 10

ER -

Direct Azidation of Adamantane and Norbornane by Stable Azidoiodinanes

Abstract

Bibliographical note

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